Diethyl Ether → HCID 86660325, compound

HRID 469467Notes

Reaction equation

HRID 469467 reaction equation
[S:1]1[CH:5]=[C:4]([C@H:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2.[Cl:29][CH2:30][C:31]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)=[O:32].C(OCC)C>C(OCC)(=O)C>[Cl-:29].[S:1]1[CH:5]=[C:4]([C@H:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N+:12]([CH2:30][C:31](=[O:32])[C:33]4[S:34][CH:35]=[CH:36][CH:37]=4)([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27579252-(Chloroacetyl)thiopheneHCID 58556996HCID 58556996, compound

Product 1

HCID 86660325HCID 86660325, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((R)-quinuclidin-3-yl) 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (diastereomer 2 of C19) (62 mg, 0.16 mmol) in ethyl acetate (3 ml), was added 2-chloro-1-(thiophen-2-yl)ethanone (25.4 mg, 0.16 mmol), and the reaction mixture was stirred at r.t. overnight. Diethyl ether (10 ml) was added, and the precipitate was filtered and dried under vacuum to obtain (R)-3-((S)-2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (75 mg, 86% yield).

Workup

  1. filtrationthe precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-05ec718611464ad69d76d8224f310435
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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